November 4, 2018 When I was applying to college some years ago, one of my teachers asked me if I thought I would regret not applying to more prestigious schools, making the observation that it's not whether the professors will be good--professors are good everywhere--but the quality of the student body. Would I learn from my peers? I hadn't thought of that conversation in a decade, but it floated up through the layers of memory recently when someone asked why I originally joined Stripe.

October 15, 2018 A couple months before graduating as one of ten students in Centre College's computer science program, I did the natural thing: applied to the JET Program to teach English in Japan. Five months later in early August I arrived alarmed and alone in Kamioka-cho, Hida-shi, Gifu-ken, Japan, but my favorite story about the JET Program is actually the the prelude: my final interview round in Atlanta.

October 14, 2018 I was recently reflecting on a strange experience I had when leading Uber's SRE team, which was being asked by an senior engineer on the mobile development team to prioritize setting up and managing their mobile test clusters. At the time, most of my attention was focused on how we could clarify better interfaces around the services we provided, eventually ending with a service cookbook, but as I reflect on it now, what comes to mind is something else entirely: how frequently teams and organizations make resourcing decisions that at least initially come across as entirely implausible.

October 1, 2018 Although it's not universally true, I've found that as folks move into more senior roles, they spend a lot more time writing. The nature of these documents vary depending on your role--strategies, presentations, memos, announcements, email, etc--but your written word often becomes your most important medium of communication. I'm fortunate to have spent a lot of time writing over the past decade, in addition to attending a liberal arts college, so this shift has generally has been something I've enjoyed.